Asymmetric alkylation of diarylmethane derivatives

Design and Synthesis of C2-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids

“…The following compounds have been previously reported and their spectra were consistent with that of the published data: Pivanilides 14 , 15 , 20 , 21 ; 6,10 anilines 16 , 6 28 , 13 aryl bromide 17; 21 and diphenylsilylether 31 . 22 …”

“…By conducting the DTR in methyl tert -butyl ether (MTBE) rather than diethyl ether and employing methyl iodide rather than methyl tosylate as the electrophile, we were able to obtain 15 in 89% yield and 95:5 er, improved from 41% yield and 78:22 er. 6 The improved enantioenrichment obtained by solvation with MTBE was first noted by Beak with the same substrate, 14 , although a methylating electrophile was not included in the scope. 7 Furthermore, the hydrolysis conditions employed below differ from those published by the Hussain group, which removed the pivaloyl group in THF using LiAlH 4 .…”

Chiral Inductive Diastereoconvergent Allylation Reactions of Allyltrimethylsilane and Diastereomixtures of Diarylmethanols Catalyzed by FeCl3

“…4,4‐Diaryl‐1‐butenes 7 are considered to be versatile key intermediates for the syntheses of these compounds and are easily obtained by the direct allylations of diarylmethanols 6 with allyltrimethylsilane using Lewis acid or Brønsted acid catalysts [Scheme , part (a)] , . Hence, many reactions for the syntheses of 7 have been developed to date; however, because the reported reactions proceed in an S N 1 manner through carbocation intermediates, the expansion of this methodology to asymmetric targets remains challenging.…”

Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes

“…Considering the diarylmethine moiety is of biological interest to our laboratory 24 and difficult to prepare in an enantiomeric enriched form, 25–29 we became interested in the development of an enantioselective variant of the Pd-catalyzed conjugated alkene hydroarylation reaction. Herein, we report our progress toward the development of such a reaction.…”